1,3-Propanediamine → HCID 57436515, compound

HRID 502578Notes

Reaction equation

HRID 502578 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:18]=[CH:17][C:12]2[C:13](Cl)=[N:14][S:15][C:11]=2[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[NH2:20][CH2:21][CH2:22][CH2:23][NH2:24]>>[NH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:13]1[C:12]2[CH:17]=[CH:18][C:9]([S:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:8])=[O:7])=[CH:10][C:11]=2[S:15][N:14]=1

Participants

4

Reactant 3

HCID 4281,3-PropanediamineHCID 962WaterHCID 58727077HCID 58727077, compound

Product 1

HCID 57436515HCID 57436515, compound

Procedure

A solution of N-tert-butyl-3-chlorobenzo[d]isothiazole-6-sulfonamide (278 mg, 0.9 mmol) in 1,3-diaminopropane (1 mL) was allowed to stir at room temperature for 3.5 h. The reaction mixture was then poured over water (10 mL), extracted with ethyl acetate and the combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give, upon trituration with ethyl ether, 3-(3-aminopropylamino)-N-t-butylbenzo[d]isothiazole-6-sulfonamide (242 mg). 1H NMR (300 MHz, CD3OD): 8.54 (dd, 1H), 7.95 (d, 1H), 7.94 (d, 1H), 3.58 (t, 2H), 2.80 (t, 2H), 1.91 (q, 2H), 1.20 ppm (s, 9H). MW=342 confirmed by LC-MS, tr=8.14 min (Method Y) MH+=343.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cfa2b04a274a470c92e2cb119583a278
Source dataset
uspto-grants-2010_08
Patent number
US07776847B2

Reaction notes

Loading…